You can and should wear high tops with shorts, but you need to do it the right way. This applies to both men and women. The fashion looks to the streets by storm in the 1980s and a resurgence in the fashions from that decade has Millennials trying to style this look. Although these shoes began as basketball shoes, you do not have to style them as such.
A few fashion rules exist for this look, but they’re really easy to learn. These rules apply to wearing these shoes with shorts for both genders whether tailored shorts or denim shorts.
A high-top sneaker look works best with high-waisted shorts. These waist cuts have a bad rap among teens and 20-somethings since they got the misnomer “mom jeans” or “mom shorts.” This may have come from some middle-aged woman exclaiming that those cuts of jeans were in style when she was in high school or from the fact that they probably snapped up the retro look when it first hit the stores again.
Here’s the truth. They have only been called that for the past four or five years and until that time the fashion world simply referred to them as high-waisted or high-rise jeans. (There are also mid-rise and low-rise jeans.) So, give up the hate for high-rise shorts and jeans, please.
They make your legs look longer and provide the perception of slenderizing the body by making a person’s legs appear longer than they are. This is a good thing, so stop the hate against this time-honored fashion look.
The shorts worn with high tops should have a fitted look. The top or shirt should have a looser design. The 1980s had this perfected. Fitted, dressy shorts with a boxy top.
Oversized sweatshirt with high-waisted, cuffed shorts. Done a pair of Converse sneakers with them and you have a perfect pairing. You can go in pleated shorts or without pleats.
Bermuda shorts, chino shorts, walking shorts, etc. all provide an option. They should exhibit a fitted cut though rather than having belled or wide legs.
Whether you choose thin or thick high tops depends upon the rest of the outfit. In general, thin high tops pair well with dressier shorts. Thicker high tops pair well with sportier looks such as basketball shorts.
Those cuffed, mid-thigh shorts you have with the pleated front? They will look best with a pair of thin Converse shoes in the high-top variety.
Your high-top sneakers should contrast with the shade of your shorts. This means if you wear light-colored shorts, such as white or cream, you should choose dark-colored high tops such as black or brown. This offset provides a color balance.
So, when you throw on a pair of black shorts, choose your white Chuck Taylor high tops. Remember: white/black, black/white, cream/brown, brown/cream, red/pink, pink/red, etc. From the latter, you should also discern that you can contrast within the same color family, so if you choose a navy blue short, pair it with a light blue high-top sneaker.
When wearing a pair of light blue shorts, pair those with a dark blue or navy-blue pair of high-top sneakers.
Your shoes must remain clean. The joy of owning a canvas sneaker is you can throw them in the washing machine to get clean. They can go through the dryer, too. Use tumble setting for best results, so you do not shrink your canvas or cause undue wear and tear on them.
With respect to leather high-top sneaks (their 80s nickname), you must polish your shoes. Whatever color you purchase, you buy shoe polish plus leather cleaner. You use it at least once every two weeks on the shoes or as needed to make them look new.
Matching remains important. While your sneaks need to contrast from your shorts, they should match your top or shirt. That does not limit you to only wearing solid colors.
As long as you choose a shirt with the same color in it as your shoes, you’re good to go. You could wear a paisley top or a plaid shirt and as long as it contains the same color as your sneakers, you match. The matching is good. It’s fashionable. It’s encouraged.
Like the Nike ads say, “Just do it.” If you want to rebel, pick some wild underwear that no person can see. With respect to that, men, pull up your pants. Who knows why that ever became a style, but no one actually wants to see your underwear under your jeans.
Please, pull your pants up. Purchase pants that genuinely fit you. They should show off your butt shape without actually showing any part of your buttocks. Seriously, you know that you purchased the appropriate fit of pants or shorts when the waist hits at your waist and you look in the three-way mirror and can discern the shape of your rear end.
This remains true for women and men. Guys miss this fact far too often. A person walking behind you should be able to tell if you have a “cute butt” or not.
If you cannot tell your butt shape in the pants, they DO NOT FIT you. You should only wear high-top sneakers with fitted shorts, so this becomes vitally important to your styling. Your shorts must fit you appropriately.
Exceptions to Styling High Top Sneakers with Shorts
You do not always have to wear high waisted shorts with these sneakers. You can also choose a mid-rise short, but when you wear this look you need to only wear a fitted top with the shorts. This diverges from the above rules in relationship to tops, but the reason for it is simple.
When you move to wear a lower rise short, you shorten the amount of material. This changes the appearance of where your waist occurs. That makes your legs appear shorter. To balance this, you need to wear a fitted top because the loosely fitted tops and shirts only look good with the high-waisted, fitted bottoms.
When women choose to wear a skort, a pair of shorts with a skirt over it that are sewn together as one piece, special styling applies. At this point, to all the other people, you appear to wear a skirt, so you must style the outfit as if you’re wearing one. That means you have to balance the skirt with your actual leg length.
If you have short legs, wearing a mini skort will only make your legs appear shorter when you pair them with high-top tennis shoes. You need a skort of a midi-length at a minimum if you have shorter legs. Women with long legs can wear any length of skort.
Beware of how you style mini skorts. If you wear a white or other solid color t-shirt with a mini skort and high tops, you will affect the look of a middle schooler’s outfit. Think Catholic schoolgirl look without necessarily wearing plaid.
In conclusion, wearing shorts and high tops can be done. Both men and women can create fashionable looks from this, but you must carefully style these shoes when mixing them with shorts. You can mix them with most lengths of shorts but pairing them with a low-rise pair of shorts only works if you have long, lean legs and a slender build.
Tall people can pair low-rise shorts with high-top sneakers, but they are the only ones.
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